Potassium Carbonate → tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylate

HRID 1523397Notes

Reaction equation

HRID 1523397 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:25][CH2:24]1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidine

Product 1

HCID 23019443tert-Butyl 4-(4-cyanophenoxy)piperidine-1-carboxylateYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy benzonitrile (15 g, 0.126 moles), potassium carbonate (28.89 g, 0.208 moles) and 4-(Toluene-4-sulfonyloxy)piperidine-1-carboxylic acid tert-butyl ester (57.62 g, 0.162 moles) in dimethylformamide (150 mL) was stirred at 100° C. while monitoring the progress of the reaction by thin layer chromatography. After completion of reaction, the reaction mass was quenched on to water (400 mL) and extracted with ethyl acetate (3×300 mL). The resulting ethyl acetate layer was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to obtain the crude residue, which was further purified by flash chromatography using (ethyl acetate:hexane, 1:9) to afford the title compound 21.25 g

Workup

  1. customthe progress of the reaction by thin layer chromatography
  2. customAfter completion of reaction
  3. customthe reaction mass was quenched on to water (400 mL)
  4. extractionextracted with ethyl acetate (3×300 mL)
  5. washThe resulting ethyl acetate layer was washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain the crude residue, which
  9. customwas further purified by flash chromatography

Sources & evidence

ORD record
ord-183d87911507468d9d136c8a0a11db78
Source dataset
uspto-grants-2015_07
Patent number
US09079888B2

Reaction notes

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